Desonide

• CAT Number: A001020
• CAS Number: 638-94-8
• Molecular Formula: C24H32O6
• Molecular Weight: 416.5
• Purity: ≥95%
• Target: Glucocorticoid Receptor
• Solubility: >20.9mg/mL in DMSO
• Storage: -20°C
• IUPAC Name: (1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
• InChI: 1S/C24H32O6/c1-21(2)29-19-10-16-15-6-5-13-9-14(26)7-8-22(13,3)20(15)17(27)11-23(16,4)24(19,30-21)18(28)12-25/h7-9,15-17,19-20,25,27H,5-6,10-12H2,1-4H3/t15-,16-,17-,19+,20+,22-,23-,24+/m0/s1
• InChIKey: WBGKWQHBNHJJPZ-LECWWXJVSA-N
• SMILES: CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4C(CC3(C2(O1)C(=O)CO)C)O)C)C

Desonide(CAS: 638-94-8) is a synthetic glucocorticosteroid for topical use, with anti-inflammatory activity. Desonide binds to glucocorticoid receptors in the cytoplasm, and the ligand-receptor complex is translocated as a homodimer into the nucleus, where transcription activation via glucocorticoid response elements within glucocorticoid-responsive genes occur. This agent induces transcription of genes coding for anti-inflammatory proteins, including lipocortin-1, interleukin-10, interleukin-1 receptor antagonist and neutral endopeptidase. Increased synthesis of lipocortin-1 has an inhibitory effect on phospholipase A2, which in turn inhibits the release arachidonic acid, thereby controlling the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.

Desonide is triamcinolone acetonide with hydrogen instead of the fluorine substituent at position 9. A corticosteroid anti-inflammatory, it is used topically as a cream, ointment or lotion for the treatment of various skin disorders. It has a role as an anti-inflammatory drug. It is an 11beta-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a corticosteroid, a cyclic ketal, a 3-oxo-Delta(1),Delta(4)-steroid and a primary alpha-hydroxy ketone.

Desonide is a Corticosteroid. The mechanism of action of desonide is as a Corticosteroid Hormone Receptor Agonist.

Overview of Clinical Research

Originator: 3SBio
Class: Anti-inflammatories; Glucocorticoids; Pregnadienetriols; Small molecules
Mechanism of Action: Glucocorticoid receptor agonists; Immunomodulators
Orphan Drug Status: No
New Molecular Entity: No

Reference

[1]. Drugs Today (Barc). 2008 Jan;44(1):55-62. doi: 10.1358/dot.2008.44.1.1143847.
Desonide foam: a review.
Parish D(1), Scheinfeld N.
Author information: (1)Pennsylvania Hospital, University of Pennsylvania, Philadelphia, PA, USA.
Desonide foam is a newly approved topical corticosteroid preparation of 0.05% desonide. It has been shown effective compared with vehicle placebo in the treatment of mild-to-moderate atopic dermatitis in both pediatric and adult populations. Given the favorable safety profile of all other desonide preparations and their utility as a low potency corticosteroid, desonide foam promises to be a useful addition to the armamentarium, when other desonide vehicles might be less acceptable.
(c) 2008 Prous Science, S.A.U. or its licensors.
DOI: 10.1358/dot.2008.44.1.1143847 PMID: 18301804 [Indexed for MEDLINE]

[2]. Expert Opin Investig Drugs. 2008 Jul;17(7):1097-104. doi: 10.1517/13543784.17.7.1097.
Desonide: a review of formulations, efficacy and safety.
Kahanek N(1), Gelbard C, Hebert A.
Author information: (1)Department of Dermatology, University of Texas-Houston Medical School, 6431 Fannin, Houston, TX 77003, USA.
BACKGROUND: Desonide is a low-potency topical corticosteroid that has been used for decades in the treatment of steroid-responsive dermatoses. The favorable safety profile of this topical agent makes it ideal for patients of all ages. OBJECTIVE: This article provides a review of desonide's history, pharmacodynamic properties, vehicle technology, efficacy and safety. METHODS: Randomized controlled trials, as well as open-label and non-comparative studies, case series and reports, experimental models, and data from the Galderma pharmacovigiliance program were reviewed in order to address the clinical efficacy and safety of desonide. RESULTS/CONCLUSION: Clinical efficacy and safety have been proven in multiple clinical trials. In addition to cream, lotion and ointment formulations, the recently developed hydrogel and foam preparations have increased desonide's versatility and patient tolerability.
DOI: 10.1517/13543784.17.7.1097 PMID: 18549345 [Indexed for MEDLINE]

[3]. J Drugs Dermatol. 2004 Jul-Aug;3(4):393-7.
Overview on desonide 0.05%: a clinical safety profile.
Wong VK(1), Fuchs B, Lebwohl M.
Author information: (1)Department of Dermatology, Mount Sinai Medical Center, New York, NY 10029-6574, USA.
Desonide (as a cream, ointment, or lotion formulation) is widely used for the treatment of steroid-responsive dermatoses. This paper provides information on its safety record, as determined from adverse event reports and published trial results. A pharmacovigilance program, initiated in 1992 for all countries where desonide is available, collected reports of adverse events associated with topical desonide over nine years. Published accounts of randomized, controlled trials of desonide in comparison with hydrocortisone were reviewed. Sixty-two reports have been collected; most were from consumers and were not medically substantiated. There were no serious reactions directly attributable to desonide treatment and the majority of events reported were classified as expected local reactions, generally mild in nature. This level of reporting is against a background of extensive prescribing of desonide; almost one million packs are dispensed per annum in the US alone. The excellent safety profile of desonide revealed by this pharmacovigilance program is supported by a review of published clinical trial results.
PMID: 15303783 [Indexed for MEDLINE]

[4]. Skinmed. 2007 Sep-Oct;6(5):241. doi: 10.1111/j.1540-9740.2007.07319.x.
Desonide gel.
Scheinfeld NS(1), Parish DH.
Author information: (1)St Luke's-Roosevelt Hospital Center, New York, NY, USA.
DOI: 10.1111/j.1540-9740.2007.07319.x PMID: 17786103 [Indexed for MEDLINE]

[5]. J Am Acad Dermatol. 2008 Aug;59(2):334-40. doi: 10.1016/j.jaad.2008.04.019.
Desonide foam 0.05%: safety in children as young as 3 months.
Hebert AA(1); Desonide Foam Phase III Clinical Study Group.
Collaborators: Barba A, Dinehart S, Gold M, Hebert AA, Jarratt M, Loss R, Maloney JM, Pariser D, Stein-Gold L, Swinyer L, Tschen E, Jones-Wu S.
Author information: (1)Department of Dermatology, The University of Texas Medical School at Houston, Houston, Texas 77030, USA.
BACKGROUND: Desonide 0.05% was recently developed in an emulsion foam formulation. OBJECTIVE: The safety of desonide foam 0.05% in children aged 3 months to 17 years was evaluated in two phase II studies and one phase III study. METHODS: A phase II open-label study of the effect of desonide foam 0.05% on the hypothalamic-pituitary-adrenal axis was evaluated in pediatric and adolescent participants with mild-to-moderate atopic dermatitis. The phase II and III clinical efficacy studies evaluated adverse events. RESULTS: At the end of the 4-week treatment in the phase II study, 4% (3 of 75) of participants experienced mild, reversible hypothalamic-pituitary-adrenal-axis suppression. The combined safety data from the phase II and III studies revealed 6% of participants in the desonide foam group and 14% in the vehicle foam group reported adverse events (P = .0002), with application site burning as the most commonly reported adverse event (3% in the desonide foam group vs 7% in the vehicle foam group; P = .004). LIMITATIONS: The studies evaluated short-term use only. CONCLUSION: Desonide foam was safe and well tolerated in participants as young as 3 months.
DOI: 10.1016/j.jaad.2008.04.019 PMID: 18638631 [Indexed for MEDLINE]